So, Self-Made Man by Norah Vincent was ...
both worthwhile and slightly disappointing.
And I can't really blame her for the second adjective. She's a very good writer: honest, funny, and engaging. She also clearly conceived of this as more than dressing up in a gorilla costume for a backstage tour of the Binary Zoo [tm Riki Anne Wilchins]. As a woman commonly seen as masculine, a dyke, a person with a degree in philosophy and more than a passing acquaintance with feminism, she frames this project (spending sixteen months moving through male spaces as Ned, for those who aren't familiar with the book) very consciously. She is very careful not to generalize her experiences to male-born men or transmen, and not to let the reader make those errors either. She picked interesting forums--a working class bowling league, a high-stress firm of door-to-door salespeople, a monastery, a men's movement group--and she doesn't let herself off the moral hook for deceiving the people Ned meets (almost everyone Ned makes a connection with, Norah eventually tells the truth to).
It's mostly the insights she gains into the lives of men that left both her and me with a vague "huh" feeling. The world of men, as she witnesses it, is not shockingly different from stereotypical conceptions. The men in her bowling league are more welcoming to Ned and forgiving of his ineptitude than any of the catty female tennis players Norah trained alongside. Strip-clubs exist so that men can find relief for the more base sexual urges they would never subject their wives to. The thirty-something women she dates are self-absorbed, rude, and automatically assume Ned embodies all the asshole qualities of their past lovers--and so he does. The church teaches its men of the cloth to ruthlessly stamp out any femininity, emotional neediness, and even intense platonic connection in each other for fear of straying toward homosexual feelings. Success in a competitive workplace plays out in a way only barely metaphorical to competition over sexual prowess, fostering intense anxiety, sexism, and chauvanism in the men who pursue it. And men are emotionally crippled by the hegemonic notions of masculinity they must live up to, which are exascerbated by the conflicting roles of "strong yet sensitive" they are currently required to fill.
I'm generalizing, of course; the specific experiences Ned has are nuanced and fascinating, extending much beyond the vague conclusions Norah cautiously skirts. But neither she nor the reader know quite what to do with these generalizations; they apparently pass the test of experience, and it's hard to know what to make of that.
The most interesting insights, by far, are those Norah has as a result of moving between gender roles. She isn't constantly in drag for these sixteen months; besides "coming out" to Ned's closer acquaintances, she spends her time out of Ned's spaces as herself, with her own identity and relationship. While it's inevitable that Norah bleeds into Ned, through violations of masculine codes of conduct, Ned also comes to bleed into Norah. Her most interesting interactions are those she has, still in Ned's body and clothes, after coming out as Norah. And eventually, the efforts of occupying two distinctly different gender spaces, becomes profoundly distressing and destabilizing for.
In summary, this book is worth at least checking out from your library. If you were worried about running into anything offensively anti-trans or essentialist, you're safe--she's smarter and more aware than that. Many of Norah's experiences as Ned (or Norah-as-Ned) are totally fascinating, and even though this book doesn't furnish the explanations you might secretly hope for, it brings some interesting observations to the table.